Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine
We report an asymmetric synthesis of (-)-Levetiracetam (1) in six steps starting from versatile new chiral N-sulfinimine (3). The key step, stereoselective 1,2-addition of ethylmagnesium bromide (EtMgBr) to chiral N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, gave the corres...
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| Format: | Article |
| Language: | English |
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Wiley
2013-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2013/475032 |
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| author | K. Chandra Babu R. Buchi Reddy E. Naresh K. Ram Mohan G. Madhusudhan K. Mukkanti |
| author_facet | K. Chandra Babu R. Buchi Reddy E. Naresh K. Ram Mohan G. Madhusudhan K. Mukkanti |
| author_sort | K. Chandra Babu |
| collection | DOAJ |
| description | We report an asymmetric synthesis of (-)-Levetiracetam (1) in six steps starting from versatile new chiral N-sulfinimine (3). The key step, stereoselective 1,2-addition of ethylmagnesium bromide (EtMgBr) to chiral N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, gave the corresponding sulfonamide (2) in high diastereoselectivity. Simultaneous deprotection and deacetylation followed by NaIO4 cleavage and reduction gave β-amino alcohol (6). Subsequent reactions yielded the targeted compound levetiracetam (1). |
| format | Article |
| id | doaj-art-2c0e5d9f4eee4ce1aeb7b9223726ffba |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-2c0e5d9f4eee4ce1aeb7b9223726ffba2025-02-03T01:01:11ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/475032475032Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-SulfinimineK. Chandra Babu0R. Buchi Reddy1E. Naresh2K. Ram Mohan3G. Madhusudhan4K. Mukkanti5Department of Research and Development, Inogent Laboratories Private Limited, 28A, IDA Nacharam, Hyderabad 500 076, IndiaR&D Centre, Orchid Chemicals & Pharmaceuticals Ltd., 476/14, Sholinganallur, Chennai 600 119, IndiaDepartment of Research and Development, Inogent Laboratories Private Limited, 28A, IDA Nacharam, Hyderabad 500 076, IndiaDepartment of Research and Development, Inogent Laboratories Private Limited, 28A, IDA Nacharam, Hyderabad 500 076, IndiaDepartment of Research and Development, Inogent Laboratories Private Limited, 28A, IDA Nacharam, Hyderabad 500 076, IndiaCentre for Pharmaceutical Sciences, Institute of Science and Technology, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad 500 072, IndiaWe report an asymmetric synthesis of (-)-Levetiracetam (1) in six steps starting from versatile new chiral N-sulfinimine (3). The key step, stereoselective 1,2-addition of ethylmagnesium bromide (EtMgBr) to chiral N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA, gave the corresponding sulfonamide (2) in high diastereoselectivity. Simultaneous deprotection and deacetylation followed by NaIO4 cleavage and reduction gave β-amino alcohol (6). Subsequent reactions yielded the targeted compound levetiracetam (1).http://dx.doi.org/10.1155/2013/475032 |
| spellingShingle | K. Chandra Babu R. Buchi Reddy E. Naresh K. Ram Mohan G. Madhusudhan K. Mukkanti Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine Journal of Chemistry |
| title | Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine |
| title_full | Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine |
| title_fullStr | Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine |
| title_full_unstemmed | Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine |
| title_short | Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine |
| title_sort | enantioselective synthesis of antiepileptic drug levetiracetam synthetic applications of the versatile new chiral n sulfinimine |
| url | http://dx.doi.org/10.1155/2013/475032 |
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